1H,1H,2H,2H-Perfluorooctyldimethylchlorosilane → HCID 86663263, compound
Reaction equation
[F:1][C:2]([F:25])([C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])Cl.[C:26]([Mg]Br)#[CH:27]>C1COCC1>[F:1][C:2]([F:25])([C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH2:3][CH2:4][Si:5]([C:26]#[CH:27])([CH3:8])[CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In an oven-dried 250-mL round bottom flask, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyldimethylchlorosilane (9.67 g, 21.9 mmol) was dissolved in 20 mL anhydrous THF. Ethynylmagnesium bromide (50 mL, 25 mmol, 0.5 M in THF) was added and the mixture was heated to 60° C. for 12 hr. After allowing the mixture to cool to room temperature, the reaction was quenched by the dropwise addition of water, followed by the addition of dilute sulfuric acid to dissolve the magnesium salts. The organic layer was separated, washed with water (3×20 mL) and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product was purified by chromatography on silica gel using hexane as an eluant. Removal of solvent yielded 9.0 g (21 mmol, 96%) of the product as a colorless liquid. Analysis of the colorless product provided the following data: 1H-NMR (200 MHz, CDCl3) δ=2.4 (s, 1H), 2.1 (m, 2H), 0.8 (m, 2H), 0.2 (s, 6H).